


No Regrets

by damnndean



Category: Supernatural
Genre: F/M, Oral Sex, Sex, Sexual Content
Language: English
Status: Completed
Published: 2014-09-28
Updated: 2014-09-28
Packaged: 2018-02-19 03:41:15
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 10,721
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2373200
Author URL: https://archiveofourown.org/users/damnndean/pseuds/damnndean
Summary: <blockquote class="userstuff">
              <p>After finally ending things with my deadbeat boyfriend I go to a local bar looking for a good time. When I meet Dean Winchester I got more than I could ever imagined. (Not the best at doing summaries.)</p>
            </blockquote>





	1. Nice To Meet You

**Author's Note:**

> **In this story it's just after they stopped the Apocalypse and that's that. The boys are trying to get back to their old way of life of "saving people, hunting things, the family business." They have a some time to kill so why not kill it and have a little fun while they're at it?**
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> **I would love to know what you guys think! If you like these 4 chapters and would like me to go further into this story let me know. I have ideas but I don't want to do it if no one likes it.**
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> **Enjoy ;)**

"You know what Todd? I don't fucking need this anymore. Get out of my apartment you free-loading, good for nothing-" I was cut off by him slamming the door on his way out.

I recollected my thoughts and steadied my breathing before letting everything sink in. Todd and I have been together for two years and during this time just about nothing good had came from it. And I was sick of it. After this past 3 months of him being without a job, not helping clean the apartment that I pay for, inviting his friends over and always making even more of a mess it was an easy decision for me to kick him out.

I walked into my kitchen and grabbed a wine bottle, made quick work of the cork and poured me a stout glass. Downing the entire thing in a matter of seconds, I poured me a fresh glass. I decided to gather up all of Todd's stuff, put it in the hallway so I wouldn't have to see him again anytime soon. I grabbed my wine glass and a trash bag from under the sink and headed into my room.

I glanced around the room seeing mostly everything is mine. What could I expect? I practically bought almost all of his clothes for him too. I made quick work of the bedroom and connected bathroom. Tugging the bag behind me I decided I needed another refill of my wine. This time I took the time to enjoy the wine and decided to make a call. I grabbed my iPhone from the counter, looked under recently dialed and hit "Ash" in my phone before pulling it to my ear. While waiting on my best friend Ashleigh to answer I drank a few more sips of the delicious Merlot.

"Helloo?" My peppy blonde best friend answered.

"We're going out tonight." It wasn't a question, it was a fact.

"What?! Please tell me this means what I think it does?"

"I kicked Todd out, and I'm getting all of his junk together right now. Which means we are getting fucked up tonight. If that's what you were thinking then yes." I smiled knowing she had wanting me to leave him this entire past year. It was probably the best news I could have delivered to her.

"Yes! There's the Cat I grew to love! I'll be there in an hour. You better look hot when I get there! We're getting you laid tonight, bitch!" I had to pull my phone from my ear to not bust an ear drum from her yelling.

There was no sense in responding I knew she had hung up. Ash and I had been friends our entire lives, we met in the 1st grade and up until I met Todd when I was 23 we had never really been apart for more than a few days here and there. Now I'm 25 and single and apparently Ash is getting me laid tonight. I just laughed at the thought, she knew me better than that. I wasn't one to do one night stands. Don't get me wrong I had my wild days back in my early 20's but it just wasn't me. After this past two years of pretty boring, very mediocre sex the idea of getting with someone else did sound exhilarating.

I grabbed an empty box I had put away just incase something like this ever happened and put the few remaining things that Todd could even possibly call "his" into the box. I opened the door and starting putting all of his stuff in the hallway. I picked up my phone and quickly typed up a text to him.

**All of your stuff is in the hallway, I'll be gone in an hour. Your stuff needs to be gone by the time I get back.**

I found the name of the intended recipient and quickly sent the text. I didn't even want to see his response so I just sat the phone down, forgetting all about it.

After finishing off my last glass of wine I decided to go get ready. Since I had just showered before deciding to kick my worthless boyfriend to the curb I just needed to fix my hair, do my make up and find an outfit. Oh god what was I going to wear? I hadn't thought this far ahead, I just knew I wanted to go out and have some fun.

I decided to do something different and curl my hair. My shoulder length jet black hair was board straight and it was always easier to just let it do as it pleased. It looked decent considering I next to never do my hair anymore. I started on my make up with a little base and powder followed by bronzer and blush. I added some shimmery eye shadow followed by black to give me a smokey eye that would stand out. I penciled some eyeliner on the top and bottom lids to make my bright green eyes pop then brushed some mascara on my upper lid and a little on the bottom. I smeared on some nude gloss on before looking at the finished product. So far I looked good, now just to figure out what to wear.

I knew I needed to get dressed before Ash showed up or she would try to put me in a hoochie skirt and stiletto heels. After what seemed like forever I settled on something form fitting but not too over the top. I went to the full length mirror that hung on my bedroom door and looked myself over. Black felt wedges with a pair of black skinny jeans that hugged me just right. And for the top I chose a deep blue shirt that had a deep V in the front. I had my best push up bra on hoping that I could maybe get a couple free drinks out of the cleavage I had exposed.

I heard a knock at the door and knew I didn't need to keep her waiting. I opened the door to a very pleased blonde. Ash was better looking than me, everyone knew it so of course I wasn't in denial about it. I was perfectly fine with it. She was about 5'7" and with the heels she was wearing at least 5'10". Compared to my 5'3" even in the wedges I was wearing I wasn't her normal height. She was slender, I was a little curvy. She was blonde, albeit bleached blonde, I was born with a head of black hair. Ash was always so upbeat and she's always the guys first option which is what I enjoyed mostly. I prefer to be in the background mostly and one way to do that is to have Ash as your best friend.

"You look hot!" Ash exclaimed as she made her way into the apartment.

"Thanks, you look pretty hot yourself." I looked her over and of course she was wearing a very form fitting crimson body con dress paired with some nude heels.

"I know right? I saw jerk-off's stuff is in the hallway, is he coming to get everything soon? If so we need to go, I'm not even trying to see him at all. And if you see him you will change your mind, and that is NOT happening!"

I couldn't help but laugh, she knew me so well. Sure I seemed confident in leaving him, but he was, well, easy. It just always seemed like the better option to stick with him rather than even attempt to move on. But she was right, I didn't want to see him. I was beyond ready to go out, with almost a full bottle of wine in me my buzz was offering me up more courage than normal. So without even responding to her I grabbed my purse and slung it over my shoulder.

"Well let's go then!" I said in my most excited tone as we left the apartment.

The bar was loud, dark, and filled with mostly men which was to be expected. "Blake's Bar and Grill" was a place we always went to when we weren't sure where else to go back in the day so we decided to see if it had it's same charm. I wasn't sure if we should sit in a booth or try to get a pool table but before I even began to speak I saw Ash walk ahead of me.

"C'mon, let's go sit at the bar." She said over her shoulder.

I never really liked sitting at the bar any more made me feel as if it seemed that I was trying too hard to look available. But if I knew anything about Ash I knew she would flirt with the bartender and he would send stiff drinks our way and I couldn't complain about that.

We sat at the bar, there were a few open bar stools on either side of us. Most of the bar occupants were at tables, playing pool or darts, or watching the karaoke that was happening on the opposite side of the large room.

"Good afternoon ladies, what are we drinking tonight?" The 30-something man said from his place behind the bar.

"I'll have a dirty Absolute martini." Ash said with a smirk on her face.

I couldn't help but roll my eyes by her obviously fake/sexy tone as she ordered her "dirty" martini. The bartenders eyes lingered on her for a moment before he turned his attention to me.

"I'll just take a vodka soda." I said plainly.

He just shook his head and started on Ash's martini.

I took this chance to look over the other patrons that were inhabiting the bar. There were a few cute guys, nothing overly special. I saw the front door open so I instinctively looked to see who was entering. Once my eyes adjusted I saw two guys walking into the bar. Two very attractive guys at that. I couldn't help myself from nudging Ash so she could see the pair.

The one that up front was a few inches short than the other one and had short light colored hair. It was hard to make out his face exactly since the lighting wasn't too great but I definitely noticed that was good looking with a nice body. The other had longer dark hair and I could immediately tell he was quite muscular even through the layers he was wearing. I heard the glasses being sat on the bar so I broke my gaze from the two at the door to grab my drink and checked Ash to see that she had a very satisfied look on her face. I took a big sip of the drink through my straw welcoming the after burn the vodka had on my body.

"Did you see those two?" I questioned, but I knew she had from the satisfied look on her face.

"Fuck yes I saw them. You know how much I love tall men. I'd like to be sandwiched between those two." I laughed at her abruptness. No matter how long we've been friends I could never get use to how she talked about men.

"Well I don't know about that, but I guess we chose a good bar, huh?" I said lightly before taking another sip.

"What makes this bar so much better than the other ones?" A deep and unfamiliar voice said from the left of me.

I turned my head to meet eye to eye with a pair of beautiful green-hazel eyes. I allowed my eyes to wander over the rest of this stranger's face. He was gorgeous. Strong features, nice lips, a little bit of sexy stubble on his face, that's when I realized this was the shorter man from the front. I felt myself lingering a little too long so I hurriedly looked past him to the other guy. I saw the first one smile out of the corner of my eye and I almost actually swooned as his smile.

"We're just excited about two attractive men showing up to buy us a drink." Ash said over me. I silently thanked her for speaking for me while I was slightly incapacitated by such a good looking man speaking to me. But once it dawned on me what she said I couldn't help but send her a glare.

Not that she cared, the smile never left her face. A hearty laugh came from both of the men to the left of me. "Well I guess we're both excited about finding a couple hot chicks to buy drinks for. I'm Dean, this is my little brother Sammy." He stated as he sat at the open stool beside me. I felt a breath hitch in my throat as I felt his jean clad muscular thigh graze mine. Ash shot up and moved over one, patting the now open stool for Sam to take a seat. Making it Dean, Me, Sam then Ash. I didn't like the idea of being trapped between two strangers and I'm sure that's why Ash did it. I shot her a death glare but it didn't seem to faze her at all.

"It's Sam." The other guy finally spoke up, correcting his brother.

"He doesn't look to little to me, Dean." Ash said in a flirty tone.

She leaned in close to me and mumbled, "Dibs on the big one."

I knew she said it quietly enough where the guys didn't hear her but I couldn't help but laugh, "Keep it in your pants, Ash." Which drew a laugh from Dean.

"I'm Cat, it's nice to meet you both." I said finally locking eyes with those emerald eyes again.

I quickly averted my stare to the other brother and he was staring at Ash with an almost scared look on his face. I laughed again before returning my gaze to the almost empty drink ahead of me.

"Another?" The bartender asked.

Before I could speak Dean started, "Get the girls here another round on us. We'll both take a beer, thanks."

I could hear the smile in his voice at the apparent look of displeasure the bartender was wearing. I returned my gaze to the almost empty beverage at hand. My thoughts running wild. Sure I thought we may meet a couple of guys, more likely Ash than me. But I wasn't anywhere near prepared to meet two guys that were this good looking.

"So Cat, huh? What's that short for?" Dean said interrupting my thoughts.

"Uhm, Cathleen." I said sheepishly as the bartender sat our new beverages in front of us.

"Beautiful name to go with an equally beautiful girl." He said as he rose his mug and clinked it to my glass, "Cheers." He said before smiling at me then taking a sip of his whiskey.

I just smiled at him, "Cheers." He was laying it on thick, without a doubt he was a player. Sure, he was beyond good looking but besides that I knew the only reason he was even trying to "flirt" is because he assumes I'll be easy. The ugly friend is always easier to go after than the hot one.

"So what bring you guys to town? Never seen you around before, and I would have definitely remembered." Ash said in her normal peppy tone.

"We're just traveling through actually." Sam said quickly.

"That's right, looks like we decided on the right town to stop at for the night, huh?"

My eyes went from Sam to Dean since he was speaking and I saw him looking at my lips as he finished. He licked his bottom lip a little and it looked like an involuntary movement. All of my previous thoughts dissipated as I felt a warmth building between my legs. The only thing I could do was turn my attention back to my drink and squeeze my thighs together trying to rid my feeling of desire. I was silently cursing myself for downing an entire bottle of wine before hand, it was definitely ridding me all of my inhibitions.

"Oh so you guys are only in town for the night?" I was almost surprised when I heard it was my voice that asked the question. Why did I sound almost disappointed? I'm not very good at this.

"Well it's kind of open ended, we don't have anything to hurry to at the moment." Dean explained with a look of pleasure on his face.

I decided I couldn't look at him anymore, if he smiled at me one more time I was going to have him right here in the bar. So I decided to turn my attention to the other two on my opposite side to see them in a lip lock. What's happening right now?

"That's my boy Sammy!" Dean yelled from behind me and I almost turned to look at him but I saw Sam rip himself from Ash and turn to Dean.

Sam shrugged at Dean and finished off his whiskey and Ash had a look of satisfaction on her face. It became apparent to me that one way or another that she was planning on getting some tonight. And it seemed that she had decided on this innocent bastard. Which inevitability left me with Dean in some way. So I decided to make the most of my night. I downed my drink and flagged down the bartender.

"Hi there, could you get us each a dressed shot of patron? Put them on my tab and then we will be ready to pay out. Thanks." I smirked at the bartender as he just shook in agreeance his head at my orders.

"What do you mean we'll be ready to pay out?!" Ash exclaimed in a disappointed fashion.

"Shots of Patron, huh?" Dean said ignoring Ash's outburst.

I couldn't avert my eyes this time and I looked deep into those green eyes and he looked pleased. So gave him the smile this. I watched his eyes move around my face and even down to my cleavage just for a second, he knew what he was doing.

"I just thought we could use something a little extra before we all headed back to the apartment." I added plainly.

"Oh, so we're heading back to your place now?" He sounded impressed but I didn't allow myself to look at him again.

The bartender returned with the shots and the tabs, before I could even grab the ticket Dean already pulled a wad of cash out and handed it to the man behind the bar, "I'm taking care of everything tonight."

"Yeah, sure." The bartender said in an almost annoyed tone before going off to tend to other guests.

I slid us each a shot and I saw a very excited look on Ash's face, an almost scared look on Sam's face and I turned to see Dean giving me one of his very sexy smirks. I would have normally felt bad about someone else picking up my bill but I definitely knew he wouldn't have paid for it all if he couldn't afford it.

"Thanks for that, Dean." I added before licking the salt from the rim of the glass, taking the shot then biting the lime while never letting my eyes leave Dean's. I could have swore I saw him shudder.

He quickly recovered and proceeded to follow ensuite and take his shot. He leaned in close and I caught the smell of tequila mixed with leather and almost a piney smell. "That isn't all you'll be thanking me for." He said quietly into my ear while brushing his lips across my ear.

I closed my eyes at the sudden sensual contact. I heard a giggle from behind me and it made my eyes shoot open immediately. I turned to see Sam and Ash both staring at us and Ash winked at me. I couldn't help but roll my eyes at her. I saw their shot glasses were empty. So I stated,"Well what are we all sitting around for? Let's go!"


	2. Actions Speak Louder

"What's with all the junk?" Dean questioned from behind me as I unlocked the door to my apartment.

I was pretty pissed that Todd didn't come get his stuff and that meant there was a possibility of him showing up with Dean and Sam were here. I just hoped that maybe since it was already so late he would wait until tomorrow to come get his stuff. I didn't really know what to say so I just unlocked the door and made my way in. Standing at the door letting everyone follow me in before I shut and locked the door behind me.

"That junk is Cat's ex's stuff. She kicked his sorry ass to the curb today. That's why we were out celebrating. Lucky for us we just so happened to find what we were looking for." I looked at Ash after her over-sharing to see her advancing on Sam. He looked scared with a little bit of arousal. He must not get out much, that must be his brother's expertise.

"You just broke up with him today?" Dean said in a shocked voice.

"Yeah, so?" I asked while heading into the kitchen to grab another bottle of wine to get me a glass. Before I grabbed the wine I grabbed a couple beers from the fridge that Todd had left. I said them on the bar and popped them open before handing them to Dean.

"Thanks. Here Sammy!" Dean called over his shoulder and I heard footsteps coming from behind him, presumably Sam's and Ash's

I was turned around reaching for a bottle of wine from the cabinet above my fridge. I knew I could reach it but even in the wedges I was wearing I still had to stretch for it. My fingers almost brushed when I felt a strong arm around my waist and a jean covered crotch on my ass/lower back.

"Let me get it." Dean said cooly from behind me. He was so close to me ear when he said it.

After he grabbed the wine he handed it to me but I couldn't move. I liked the feeling of how close he was to me. The liquor coursing through me, wanting me to be even closer to him. My body reacted to his touch and I pushed my ass against him. We were perfectly lined up now and I felt him growing beneath the fabric separating my skin. He pushed into me a little before pushing the hair from the right side of my neck and started placing soft, sensual kisses from my ear down my neck. I couldn't help the loan moan that escaped my lips. He knew what he was doing and it had been a while since someone touched me like this.

"Ahem.."

I heard a throat clear from behind us and it pulled me out of the trance he had put me in. I went to turn around but Dean didn't loosen his hold on me. So we ended up just being face to face. He was hold a smirk on his face and I noticed the bit of freckles he had along his nose and under his eyes since the lighting was better here and we were so close. He had wrinkles around his eyes that showed he had been through some stuff in his past. It just made me wonder if there was more than looks, albeit sexy almost godly looks, to this stranger.

"Can I just get some wine, please?" Ash begged from her spot opposite the island in the kitchen.

My eyes darted to her and if only looks could kill. She looked so pleased and Sam was sharing the same expression. Which made me wonder, I was sure they had to do this all the time. If not Sam then at least Dean with how thick he was laying it on earlier. But Sam almost seemed happy about Dean making advances on me.

Dean pulled the wine bottle from my hand and sat it on the island, "Have at it."

He crashed his lips down to mine and I continued the kiss. I felt all my worries melt away while simultaneously melting into him. Damn he's a good kisser. Is all I could manage to think as he brushed my lips with his soft tongue asking for entrance in. I opened up for him without even a second thought on it. He ran his warm tongue over mine in an expert fashion and it caused another involuntary movement of my body as I rubbed myself against his growing erection. I received a low throaty moan from him and he pushed me into the fridge. I heard some of the things that were on the fridge along with the magnet fall to the ground followed by a loud and dramatic gasp coming from somewhere else in the room.

I pushed Dean away to see Sam and Ash sitting at the bar but staring at the door. I followed their gaze and my eyes met with Todd's and I was filled with panic.

"So this is why you kicked me out? So you can have some weird foursome with your slut friend?" Todd spat out.

Before I could even cringe at him calling Ash a slut she was on her feet charging him. Sam luckily grabbed her before she was able to make it to him.

I pulled myself from Dean's firm hold he had on me. I advanced towards Todd before I got too far away Dean grabbed my arm, "You want me to handle him?" Dean said with a stern look on his face.

How is it possible that I just met this man and yet he was willing to "handle" Todd for me. Yeah, I was going to give him the night of his life later. I just gave him a wink and he loosened his hold on me.

I walked up to Todd and just stared at him for a second before opening the door that was behind him. I held out my hand, "Give me your key."

"I'm not gi-" That's when my fist connected with his nose and God did it feel good. After these years I had wanted nothing more than to do what I had just done.

He doubled over and grabbed his nose with both hands. He looked at me with a shocked expression before he hurriedly took his key from his key ring. "Here you go you crazy bitch.", he murmured while throwing the key down. He said something else but I couldn't me it out through the hand on his nose that muffled his words. He turned around and slammed the door behind him. I locked it behind him and turned to see everyone looking at me.

"What?" I asked innocently before laughing and heading back over to grab me a glass of wine.

"That was awesome!" Dean yelled excitedly.

I couldn't help but laugh at him, "It was nothing."

"Nothing my ass! You just socked that guy and he just threw you the key and left. What a little bitch." Dean finished with a laugh.

I decided to abandon the wine and took his beer from him and finished it.

"I think I'm in love, Sammy." I looked at Dean and he had look of pure arousal on his face.

Sam and Ash just laughed for a second before Ash poured her a full glass of wine, "We're going to the couch. You two have fun." I knew she must have loved watching things getting a little hot and heavy between Dean and me, she was into the idea of me getting laid for some reason.

"Take it easy on him, Ash!" I called out as they walked away and it almost seemed as if she was dragging him into the living room.

"He has no idea what's she's going to do to him." Sure I didn't know much about him or Dean for that matter but I had a feeling Sam had no idea what he was in for.

"I don't think you have any idea what I'm going to do to you." Dean seductively whispered into my ear from behind me.

I turned around to face him and I looked him in the eye, "Do your worst."

I took the initiative this time and began kissing him. I had enough confidence built up from the interaction with Todd and the lingering effects the alcohol were having on me that I knew now that if he's here he must find me attractive. If he's here now there is no need for me to worry about what will happen later, I'm just going to have a good time with this ridiculously good kissing, sexy man.

Dean wrapped his arms around me and I couldn't fight the need the be closer to him so I wrapped my legs around his strong frame. He didn't waver at all as he carried me over to the island where only a couple minutes earlier we were all innocently hanging out at and sat me on it. My legs stayed wrapped around him and I felt his now rock hard cock press on my warm center and I couldn't fight the moan that escaped into the kiss. His hands rubbed up and down my back for a bit and one stopped at the base of my neck as too deepen the kiss even more but I took this opportunity to explore his skin. I broke away from him and started placing delicate kisses down his strong jaw line.

He tilted his head encouraging me to continue. Once I made it down to kiss neck I must have hit a special place because I received a very sexy growl of pleasure from Dean. I felt his hands move under the front of my shirt so I arched my back into his touch. I felt his warm hands run over my stomach up towards my breasts. I smiled into his neck before nibbling slightly which he must have liked because he thrusted his hips towards me. I allowed my hand opposite to the side I was kissing to make it's way down is hard body and I stopped at the top of his jeans.

A quiet, "Fuck" escaped Dean's lips as I brushed the bare skin right above the top of his pants and it did nothing but make me want to keep going. My hand moved down lower over his belt buckle onto the crotch of his blue jeans. I leaned back and looked him in the face as a grabbed his hard member through the blue jean fabric. His eyes fluttered a little but the smirk on his face never wavered.

"Can you two at least take it to the bedroom? I just want another beer." Sam called from the doorway.

I didn't know what to do except lean into the crook of Dean's neck. I wasn't one for public displays of affection much less with a guy I barely know in front of his little brother but somehow I've managed to get caught in the moment twice. He pulled his hands from my shirt and stepped back pulling me with him. It took me a second for my legs to get stable under me so I didn't much. But instead of being in the crook of his neck my cheek was on his chest.

"Working on it Sammy." Dean stated sounded slightly out of breath and annoyed.

I heard Ash's giggle come from somewhere else in the room and I just knew she was loving every minute of it. I grabbed Dean's hand while shooting another hate filled glance not only to Ash but even Sam this time.

"Let's go, Dean." It's all I needed to say and he eagerly followed behind me.

My heart started to race as we made it to my bedroom door and I just stopped before I opened the door. This is really happening.. I couldn't remember the last time I had sex with someone other than Todd. What if I wasn't any good anymore? What if he didn't like what he saw when my clothes came off? My mind swirled with all of my insecurities and it made me start doubting if I should do this.

"Cat? You okay?" Dean's voice pulled me from my thoughts.

I turned to face him and he was giving me this face, like he was actually worried about me. I couldn't help but give him a smile. I leaned in and he met me halfway in an intense kiss.

I pulled away from him, "I'm more than okay."


	3. Once Is Never Enough

"Take off your shirt." I demanded once I pulled myself from his grasp.

After managing to get the bedroom door open we stumbled to the bed where I've been having the make out session of my life with this familiar feeling stranger. I kicked my shoes off and somehow he managed to get his boots off in just enough time for us to end up comfortably on the bed.

"Yes ma'am" He agreed and he sat up and pulled his shirt over his head. I swear I saw every muscle in his arm move as he tugged on the material. Once his body was cleared of cloth I had to stop myself from gasping at his body. Sure I have seen good looking body's but never one like this so up close and personal.

"Are you kidding me?" Spurted through my mouth as I ran my fingers over his chest. I noted a neat looking tattoo on his chest and absently traced my fingers around it.

He smiled at me but I almost didn't notice. It took a lot for me to rip my eyes from his body. I knew I was being overly obvious but the liquor still coursing through me made me not care too much. I was having fun.

"You're turn, baby." He said in a hushed tone before going in for another heated kiss. After a couple of minutes I felt his hands working on the bottom of my shirt so I stopped the kiss just long enough from him to pull it over my head. I went back in but Dean pulled away.

"You get to ogle me but I don't get to soak your sexy ass in? No way." He smirked before tilting his head back to get a look at me.

I felt heat raising into my cheeks, sure I tried to stay in shape but I wasn't a pencil. I have curves and no matter what I said to myself I would always be a little self conscious. I was watching his face for approval and he was pretty hard to read but by the glisten in his eye he must have at least liked what he saw a little bit.

"I'm not going to lie.. I like what I see," He paused to moisten his pouty lips, "I can only think of one thing that would make you look better."

I felt a huge amount of embarrassment. Was he talking about my body? It flooded through me so quick I almost didn't know how to recover. I knew better than to open up to a stranger like this. My hand instinctively went to my stomach, the main reason for me being body conscious. My eyes dropped as I laid back into the bed on my side, still facing Dean.

His fingers tilted my head up and he gave me a reassuring look before he started kissing at me neck. My body didn't want to open up but damn, he was good. I felt his hand working at the button on my jeans and I almost protested but before I could he pulled them off and was at the foot of the bed tugging the skinny jeans over my feet. I rolled onto my back and he was looking at me with a look of pure lust.

"Now.. You're pretty damn perfect."

I was so shocked by his words, "Wh- What?"

He ran his hand all the way up me from my ankles, up my thighs, over my panty-clad mound, which drew a moan from me. He stopped and smiled at me before pushing the hand that I had resting on my stomach away and placing a soft kiss where it had been previously.

"You heard me." His eyes flickered up to mine and I saw that same flicker in his eye.

He made his way back up me but stopped in the middle of my breasts. I went to wrap my arms around him which made pushed my breasts around his face and I heard a very satisfied, "Mmm.." come from him. I laughed a little before releasing him.

"Sorry.." I muttered, "I forget how in the way they are sometimes." I honestly admitted.

"Did you hear me complain? I don't think so." He laughed before playfully placing his face in the previous spot and with a hand on each side of my breasts he repeated the previous noise while in between them.

I couldn't help but laugh at him, somehow he was so okay with being so silly. He was so confident. It was something I admired very much. Being sort of cocky suited him.

He moved his hand to behind my back in one subtle motion. I arched my back a little as he expertly undid my bra. The straps slinked off of my shoulders and I took a deep breath and pulled the bra the rest of the way off and threw it somewhere in my room. He leaned his head up just a little to a get a full view which drew a small smile for him. He started placing small kisses all over my chest and I felt my nipples growing erect. He was being so gentle, so far he never ceased to surprise me.

I gasped as he finally took one of my soft pink nipples into his mouth. He rolled his tongue around it and I couldn't keep the low moan I had in my throat from escaping. He then pulled my taut nipple in between his teeth and tugged gently and I couldn't stand him not being inside of me anymore.

I shoved him off of me and straddled his waist and at first him seemed surprised then he smirked at me and I returned the smirk. I started kissing his neck and worked my way down his chest not missing the chance to brush my lips against his nipple which he obviously liked because I felt his body tense up under me. I smiled as I continued down his body and his hands brushed my hair out of the way so he could see my face so I looked up at him as I undid his jeans with one hand and never broke eye contact. I pulled his jeans down along with his boxers and he hurriedly kicked them the rest of the way off.

I looked down and saw his massive erection. I could feel how obvious my face was being but I wasn't going to say I wasn't a little scared. It was by far the biggest dick I had ever seen up close and it was definitely a lot bigger than what I was use to.

"Don't worry baby, I'll go easy." He said as he brushed my cheek with the back of his hand.

I shook my head before going back up him and laying at his side. He grabbed me by the back of my head and wrapped his fingers in my hair and began kissing me. The kiss quickly escalated and he turned onto his side and had his upper body over me and I felt his hand working it's way between my legs he brushed over the top of my panties and I felt myself growing wet for him. He rubbed a couple more times over my panties until I couldn't handle it. I pulled myself from the kiss and tore the last remaining bit of clothing off of myself and turned back to him.

He smiled at me, "Let's get you ready for me." He started kissing me again before I could say anything and his hand slipped back in between my thighs. He pushed my thighs open and started by softly playing with the sensitive area but I wanted more. I thrusted my hips up and he smiled into the kiss.

"Got to be patient." He said and I felt his lips brush against mine with every word.

"You're just making it hard." I said returned the sensation of my lips brushing his as I spoke.

He grabbed my hand and placed it on his thick cock, "No, you're the one making it hard."

He crashed his lips back onto mine and I moaned as he started rubbing small circles around the heat between my legs. I had been aching for his touch and now that I was getting it I wasn't sure if I could bare all the pleasure he was going to give me. He broke away from the kiss and starting it on my neck. He slid his middle finger down to my entrance and slowly entered into me. I gasped and moaned from the sudden pleasure. He began working it in and out of me and his thumb rubbed over my bud. MY breathing started to increase speed and I felt a warmth growing in my belly. He moved from my neck down to my nipple and as he pulled it in between his teeth while simultaneously sliding a second finger in. It's all it took to send me spiraling out of control. I grasped the back of his head and pulled his hair as I let moan after moan escape from my lips. He never slowed his tempo until I was coming down from the high he had just given me from that orgasm. I released him to run my hand through my hair and bring me back down to earth.

My eyes fluttered open to see that he had moved in between my legs. He was knelt back on his heels and locked eyes with me. He took the two fingers that were previously inside of me to his lips and sucked all the juices off.

"So sweet.." And I felt myself growing wetter for him by the second.

Dean reached back and grabbed his pants, he pulled out his wallet and quickly grabbed a condom out. He grabbed his hard member and slid the rubber over the tip along his thick shaft. He then rubbed the tip against my moist center. Presumably trying to get me prepared for what was coming next. I closed my eyes and braced myself for his entry but I was surprised when I didn't feel anything except a soft kiss on my lips. Once he pulled away we were face to face.

"Are you ready?" Dean asked.

I gulped, "Ready as ever." He nodded before glancing down and using his right hand to line himself up with me. He pecked my lips once more before slowly entering himself into me. I felt him going deeper and deeper. Stretching me out more and more. Then he stopped once he was fully inside of me.

"Fuck, you're so tight." He moaned and I couldn't hold my smile in.

Sure, he was bigger than I was use to but damn, did it feel good. He sat their for a moment allowing me to adjust to his size while he enjoyed the feeling of my tightness around him. He opened his eyes and looked at me looking for approval to move forward and I just grabbed his hips and started working myself from under him.

"Son-of-a-bitch.." He muttered under his breath.

And I let a small moan out and it was all he needed to take over. He brushed my hands away and grasped my hips and started moving in and out of me while steadily increasing his pace. He felt so good inside of me, each time he would go deep and deeper I wasn't sure how long I could hold on. I opened my eyes under heavy eyelids to see this beautiful man pounding away at me and it sent me over the edge.

"Oh, Dean!" I yelled while fighting back a scream.

Dean gritted his teeth and continued going at a fast pace for me through my orgasm. My hips bucked and when it was all over my body quivered. He slowed his pace a little and wiped his brow. I didn't have long to recover from the orgasm because I immediately felt an immense amount of pleasure again as he rocked in and out of me. He had already provided me with two orgasms now it was my turn to satisfy him.

I slid myself out of him and got up on my knees so we were face to face. I pushed him flat to his back, "Now it's my turn." I climbed on top and steadied him under me then slid myself onto his raging cock.

"Fuck yes!" He almost yelled as he was all the way inside of me. And I smiled down at him and gave him a passionate kiss in which he returned. I broke off the kiss and placed each of my hands on his chest and slid up all the way to the tip and slammed myself back down a couple of times. His hands were on my hips and he was trying to trust up into me.

"No, no. You just lay there." I demanded. I pulled his hands from my hips.

"Yes ma'am." He retorted happily and placed his hands behind his head.

I sat up fully with him all the way inside of me and starting riding him like I have never done in my entire life. After a matter of minutes and a few cuss words later Dean's breath started to hitch here and there.

I leaned down to make our faces only inches apart, "Do you like it when I ride your huge cock, Dean?"

I saw him gulp, surprised by my words almost as much as I was surprised by them but something felt right about talking nasty to him.

"I fucking love it, you dirty girl." He pulled my hair a little which jerked my head back and I felt my walls tighten on his dick from the hair pulling.

Dean couldn't bare it anymore, he rolled us both so he was on top. He held one of my legs up in the air as he slammed himself into me over and over. I felt another orgasm coming up soon.

His grip tightened on my leg, "I'm about to come." He panted.

"Make me come with you." I demanded and he quickly started rubbing on my clit and within a matter of seconds I was screaming his name and he was grunting and emptying everything he had but he didn't stop until my orgasm was over too.

He collapsed on the bed beside me both of us trying to catch our breaths.

He recovered first and rolled to his size to face me, "God damnit girl, I didn't know you had all of that in you."

I rolled to my side so we were face to face, "You don't even know the half of it."

I saw lust filling his eyes and he glanced down at the used condom still on his dick. "Give me 15 minutes and you'll just have to show me some more." He stood up from the bed to head into the bathroom. I gave him a hard slap on the ass and he jumped a little and turned back to me.

"Better make it 10." I insisted.


	4. I'll See You Around

**Notes for the Chapter:**

> **Final part! Let me know what you think ;)**

I woke up to a stream of light peeking around my bedroom curtain and right into my now open eyes. I groaned and rolled over hoping to avoid the light but as I went to roll from my right side to the left I felt a pair of two strong arms wrap around my waist tighter. My eyes grew wide. Wasn't he suppose to leave in the middle of the night? Isn't that how one night stands work? I questioned silently.

I was still in a fog, the effects of the alcohol still not fully gone. After a few seconds of trying to remember the day before memories of the day and night before starting filling my brain. Starting with Todd and ending with Dean and I having our third round of intense sex before finally passing out. I was almost certain I would wake up to an empty bed, the memory of Dean Winchester the only thing reminding me of the craziest night I will possibly ever have. Last night I had adrenaline and liquor fueling me, I wasn't sure how I would act once he woke up. Luckily for me a still had a small buzz going to at least help me make it through this awkward morning. The only thing I could think to do was slip off to the bathroom and maybe when I come back he'll see his chance and be gone. I assured myself that would be the case. I attempted to pull myself from his grasp but he only pulled me closer to him. It was almost sweet how he wouldn't let me go. Accepting defeat I leaned back into his strong chest.

I'll just enjoy this while I can. I thought to myself as I adjusted myself, but as I did so did he. I felt him almost thrust his hips towards me again and I felt his very hard member against my bare behind. I felt heat rising to my cheeks. Sure, we had a lot of steamy sex and we held nothing back but there was still something about Dean's naked morning wood pressing against my ass that made me blush. I also couldn't believe that he was already hard again despite the origin. The thought of going another round pulled a shudder from my body.

"Mm, somebody already misses you." Dean grumbled still half asleep while he grinded against my ass.

I gasped a little from him being so abrupt and also because deep down I liked it. I felt him press his lips against my left shoulder and place a small kiss there. I tensed from the kiss and I felt his lips turn into a smile against my should and I couldn't help but relax and smile a little too. I slowly rolled to face him and this time he allowed me to do so. Once I saw his face I swear I melted into the mattress a little. His face a little puffy from the lack of sleep, his hair jostled and in the morning light I could see small freckles along his nose and cheeks. I could even see the small golden flecks in his green eyes. He was wearing a genuine half smile that made me grateful we were already laying down because my knees would have given out.

"Good morning, baby girl." Dean said softly while brushing back my bangs that had fallen into myself and placing them behind my ear.

"Good morning." I replied sheepishly and averting my eyes from his feeling myself blush from him referring to me as 'baby girl' and him looking how he looks.

He brought his hand under my chin and gently pulled me back up to him. Only inches apart I felt my breath hitch. I watched his eyes move from mine down to my lips and I knew what was next. He placed his hand gently behind my neck and softly pressed his lips to mine. It was possibly the sweetest kiss I have ever experienced. He didn't try to take things anywhere he just kissed me.

"Are you guys seriously going at it again?" I heard an angry Ash coming from somewhere in the room.

I pulled back from Dean slowly and our eyes met for a few moments more before Dean smirked.

"Sammy!" Dean yelled in a deep voice.

Sam was there in the door and I was suddenly very aware of how naked I was. I wrapped the blankets even tighter around me insuring no one would be seeing any parts of me they didn't need to see. Dean sat up leaving his chest exposed but still had the blankets covering his bottom half. I watched as Ash looked over Dean's body and I felt a surge of jealously rip through me. I glared the best I could but she acted as if it didn't faze her too much.

"You couldn't keep her occupied a little longer?" Dean asked with a false anger in his voice. He couldn't get the smirk off of his face.

Sam's eyes narrowed at his older brother. "Well unlike you two some of us didn't really hit it off."

"And by that he means he passed out after right after you two came back here and I was stuck listening to you two go at it like rabbits!" Ash let her voice almost reach a shrill.

Sam cut his eyes from his brother to Ash. "I already said I was sorry." Sam tried to explain.

"Save it pretty boy.." Ash warned.

"I forgot to tell you, little Sammy here is a light weight some times." By the shit-eating grin on Dean's face I could tell he was beside himself with joy.

Ash looked back at Dean and threw him a smile she usually reserved for when she was seducing men and I didn't like it one bit.

"I knew I should have called dibs on you. You wouldn't have let me down. And no offense Cat but there's know what you knew what to do with all of that." Ash said as she gestured to Dean.

That's was the thing about her she always spoke before letting herself think about what she was saying. It was the reason why I loved her but it was also the reason between most of our fights. I went to sit up not happy with how my best friend was acting at the moment but Dean just put his arm out as to keep me calm so I didn't reveal to much of myself.

"Well no offense to you sweetheart, but you're not my type. And Cat knew exactly what she was doing." Dean said defensively, emphasizing the 'exactly', and I swear if I blushed one more time I was going to permanently stay red.

Ash made a face that would normally be saved if she ate something sour and with a huff she hurried past Sam in the doorway. The next thing I heard was her yelling something about seeing me later and she slammed the door. Sure she was my best friend but I thought it was hilarious Dean taking her down a couple of levels. I rolled to my side making sure the blanket was tucked firmly under my arms before I looked up at Dean. I placed my hand on his bare thigh and his eyes grew wide. I gave him a smirk, what can I say he needed to be rewarded for sticking up for me.

Dean was still sitting with his back against my headboard and my hand started working it's way up and down his thigh gently. I saw the sheet slowly starting to raise up from his growing erection and I couldn't help the smile forming on my lips.

"Dean! Seriously?" Sam said with disgust as he was trying to shield his eyes.

"Sammy, how about you go get us some coffee." Dean said sternly his eyes never leaving mine.

Sammy shuffled through the clothes on the floor searching for Dean's jeans and the keys to the Impala while still shielding his eyes. If I wasn't so turned on I would have probably laughed at how ridiculous he looked. Not waiting for Sam to leave the room I snuck under the blankets and took my place between Dean's legs. With one solid lick from the base all the way to the tip I took as much of him as I could into my mouth with one fluid motion.

"Holy shit!" Dean exclaimed while wrapping his fingers in my hair.

I heard Sam murmuring curse words but I didn't care. It wasn't like I would see either of them every again and I wanted to make Dean remember me. Dean would remember me.

I went up slowly sucking slightly as I did so before taking him back only stopping when he hit the back of my throat. I heard a low yet excited moan come from Dean and I couldn't help but to smile a little around his cock before starting a slow rhythm going up all the way then back down as far as I could. I heard my front door slamming again letting us know Sam was no longer in the apartment. Dean ripped the blankets off of us and I pulled away from him and gave him an innocent look. Dean didn't say anything but his mouth hung open like he just couldn't get the words together.

"What?" I asked keeping up my innocent demeanor.

Dean didn't say anything he just grabbed my hair and shoved his thick member down my throat making me gag a little. I pulled back and after a quick breath a smiled at him and began working my mouth up and down, up and down steadily going faster and faster. He low moans only turning me on more and making me want to please him more than anything. I added a hand into the mix allowing it to provide some extra friction and his cock twitched in my hand a little. I leaned back to look at him using my hand to go up and over the tip.

"Does it feel good?" I asked quietly before placing small kisses along his muscular lower abdomen and down his strong thighs hoping to not forget any little piece of this perfect man.

"Fuck yes it feels good." Dean just about moaned out his eyes never opening.

I stopped everything all at once making his eyes pop open. He seemed surprised that we were now eye level. I positioned myself up on my knees ready to slide onto his thickness. I grabbed it and rubbed it against my heat readying myself for entry. His placed his hands on each of my hips and his lips crashed onto mine. I kissed him back and opened up my mouth inviting his tongue in as I slammed onto him taking him fully into my already slick entrance. I felt him tense under me and I just sat there adjusting to him and enjoying the kiss. I broke from the kiss and just looked at him, lust filling his green eyes as I began to work my hips back and forth grinding on him.

"Goddamn it.. you're good at that." He said between placing small kisses all over my chest. His hands never leaving my hips and I could tell when he really liked what I was doing because he would squeeze me a little harder. I was sure I would have bruises but at the moment the pleasure outweighed the pain.

I leaned back allowing my chest to open up to him more and he took one of my nipples into his mouth and softly sucked. I couldn't stop the moan from escaping my lips and I shuddered a little. His dick was steadily tickling my G-spot, the position being perfect for that. I tried not to falter too much but the pleasure I was feeling started making it harder for me to keep my rhythm. Dean wrapped his arms around me pulling me to him and started pumping from under me. I couldn't bare it anymore, the sudden pace change sending me over the edge.

"Oh fuck.. Dean." I managed to say in between moans.

"Come for me baby." And it's all I needed to send me into oblivion.

I rode out my orgasm and Dean's breathing started to waiver, meaning he was getting close too. Once I recovered I started kissing his neck up to his ear. I nibbled on his lobe slightly and he moaned deeply, his orgasm close.

"Come in my pussy, Dean." I whispered quietly in his ear.

"Fuck!" He yelled and with one strong thrust I felt him empty all he had deep inside of me.

I laid on top of him for a while regaining my breathe and just soaking in the last few moments with him. After a bit a leaned back and smiled at him in which he returned one of his, at this point, infamous smirks. I placed one more small kiss on his lips before getting off of him and heading to the bathroom. I cleaned myself up, wiped the old make up off of my face and threw my hair into a bun. I grabbed my gray jersey robe and pulled it on before leaving the bathroom. I was greeted by a fully dressed Dean and I may or may not have pouted hoping to see his bare body once more before he leaves. I shook it off and walked up to him.

"Well, it's been fun baby girl. Too say the least." Dean said proudly.

I laughed a little and shook my head agreeing. We walked out of the room and just in time too as a really loud knock came from the door. I rolled my eyes and opened it to see Sam. He handed me my coffee.

"It was nice to meet you. The coffee is black, wasn't sure how you liked it." Sam said sweetly.

I was surprised by how nice he was being considering he just saw me in a very compromising situation with his brother.

"Thanks.. It was nice to meet you too." I said giving him the most genuine smile I could muster.

"I'll wait for you by the car, Dean." Sam said to his brother.

"Yeah, I'll be right out." He called after Sam since he already started walking away.

Dean took Sam's place at the door, "So.. I'll see you around." Dean said with a charming smile.

"Yeah.. I would like that." I said honestly.

Dean leaned down and gave me a slow and sweet kiss. He pulled away and turned to walk down the hallway. I watched him for a second before I realized neither of us even had the others number and I didn't like the idea that if he even came back to town that he couldn't reach me.

"Dean, wait up!" I yelled after him.

He stopped and turned to face me and I figured I needed to come up with something smooth so he didn't think I was being pathetic.

"I forgot to give you my number. You know, just incase you're nearby again and want to recreate the past day. You know?" I said sweetly at him trying my hardest not to stammer or blush.

"I would like that." He pulled out his phone and I quickly put my number and saved it under Cat, hoping that would be enough. I sent myself a text so I would have his number but deleted the outgoing message not needing him to know I just felt better having his number too.

I handed him back the phone, "It's under Cat.. just let me know if you're ever in Colorado again. I don't mind driving." I hoped I didn't sound too desperate.

"Sure thing, baby girl." He slipped the phone in his pocket and before I knew it he was out of sight.

I sighed a happy sigh and made my way back into my apartment. I shut the door behind me and smiled to myself knowing I just had the best weekend probably of my life. Deep down knowing that wouldn't be the last I saw of Dean Winchester.


End file.
